Reasonably Happy with Paul Ollinger

A working class kid from the poor part of Connecticut, Jared Dillian somehow managed in 2001 to land a job as a trader at Lehman Brothers, the then-prestigious investment bank. Wearing cheap suits from the Mens Wearhouse, he found himself out-of-place among the Armani-clad Ivy League set on Wall Street. But he loved trading and made a lot of money in the process. In this candid conversation, Jared...

My guest today paid a dowry of eight cows for his first wife and six cows and three sheep for his second wife. Josphat Mako, or just “Mako," grew up in Kenya’s Maasai Mara, a massive plain just north of the Serengeti. He taught himself English, learned how to drive, and has since become become a well-known safari guide for the legendary Cottars camps.  In today’s episode, we talk about his childho...

(Originally posted October, 2019) Ryan Holiday is the author of ten books, which have sold sold more than 2 million copies worldwide and been translated into 30 languages. World-class athletes, celebrities and political leaders use his lessons to achieve peak performance. His 2014 book, The Obstacle Is The Way, was read by the New England Patriots during their 2014 Super Bowl-winning season and by...

Communicator, author, and pastor Andy Stanley founded Atlanta-based North Point Ministries (NPM) in 1995. Today, NPM consists of seven churches in the Atlanta area and a network of nearly 100 churches around the globe that collectively serve nearly 185,000 people weekly. A survey of U.S. pastors in Outreach magazine identified Andy as one of the ten most influential living pastors in America. Andy...

Comedian Paul Ollinger started Crazy Money to explore the connection between money, happiness, work, and meaning through the lens of his guests' expertise and/or money journeys. Preveious interviewees include prominent authors, academics, CEOs, celebrities, and winners of the Nobel Prize, Heisman Trophy, PGA Championship, and Olympic Gold medals, including: Academics: Princeton's Sir Angus Deaton...

Nobody works harder than LL COOL J. The musician, producer, actor, and entrepreneur has been playing at the highest levels of art, business, and culture since he burst on the scene at the age of 17, in 1985. For over 35 years, LL has pushed himself to achieve in all that he does while leading with spirit and character. And achieve he has. The two-time Grammy-winner and first ever Hip Hop Kennedy C...

“Never tell anyone a secret because they will surely use it against you.” That’s what Lord John Browne’s mother, an Auschwitz survivor, always told her son. The former CEO of BP followed her advice until he was 59 years old when his secret—the fact that he was a closeted gay man—was exposed by an ex-boyfriend in the British tabloids.  The revelation resulted in a media storm and Lord Browne’s imme...

James Altucher is an author, chess master, podcaster, former hedge fund manager, angel investor, and — just to top it off —comedian. Oh, he’s also an entrepreneur who has started 20 companies, 17 of which failed. Over the course of his career, James has made and lost multi-million dollar fortunes “three or four times.”  The Wall Street Journal best-selling author of Choose Yourself, Choose Yoursel...

Rachel Greenwald is a professional match-maker whose business serves wealthy men looking for love. A graduate of Harvard Business School where she is an Executive Fellow, Rachel is also the New York Times bestselling author of Have Him at Hello and Find a Husband After 35. In today’s episode we discuss the mistakes both men and women make when talking or inquiring about money during courtship. She...

Holly Parker is one of the most dynamic people I have ever met. A top NYC realtor who has sold over $8 billion in property, she is also a self-made millionaire, consummate connector of people, world traveler, twin mom, and author. In her new book, Back on the Market: A Realtor’s Guide to Love and Life Holly tells the story of her divorce, re-entry into the dating world as an ultra-successful woman...

If you have kids in or nearing college age, you HAVE to listen to this episode. Ron Lieber’s new book, The Price You Pay for College contains critical, in-depth information about one of the most important financial decisions your family will ever make. After 15 years of financial reporting, Lieber reports that “No consumer decision inspires more confusion and emotion than the question of what to p...

Daniel Markovits is the Guido Calabresi Professor of Law at Yale Law School and the author of The Meritocracy Trap in which he outlines the price meritocracy imposes on society. In addition to severely limiting opportunities for the middle and lower classes, our knowledge-based economy “devours the elite” who work brutally long hours at top law firms, investment banks, and consulting companies. An...

William “Bill” Irvine is an author, philosophy professor, and an active investor who describes his intended audience as "intellectually-upscale readers who have a minimal background in philosophy but who are interested in carefully rethinking the assumptions of everyday life.” (Hey, that’s YOU!) Bill wants to make philosophy accessible and applicable to our everyday struggles. His research can bes...

Jesse Itzler only eats fruit 'til noon, loves Run-D.M.C., and enjoys living life "out of the box." The author of the New York Times bestseller, Living with a Seal, cofounded Marquis Jet, the world's largest private jet card company which he and his partner sold to Berkshire Hathaway/NetJets. Jesse then partnered with Zico coconut water, which he and his partner sold to The Coca-Cola Company. He’s...

The New Yorker called Princeton and University of Melbourne bio-ethicist, Peter Singer “the world’s most influential living philosopher." Time included him on its annual list of the world’s 100 most influential people. Peter has a question for you: Did you know that for the cost of a new television ($600), you can save a life? Here’s another: would it be worth foregoing a nice bottle of wine ($50)...

Tony Hsieh was the former CEO of Zappos, which Amazon bought for $1.2 billion. With a net worth reported at over $700 million, Tony appeared to have everything anyone could want. However, Tony suffered from severe addiction that pulled him down into a spiral of substance abuse, bizarre behavior, and his eventual death. During the Covid lockdown, Tony bought over $50 million worth of houses in Park...

John Helliwell is Professor emeritus of Economics at University of British Columbia and editor of The World Happiness Report, a landmark survey of the state of global happiness that ranks 156 countries by how happy their citizens perceive themselves to be. The report has been published since 2012 when the United Nations General Assembly invited countries to measure their citizen’s happiness. And w...

Kay Madati was born to a single, Tanzanian mother who died when he was 12. Kay and his brother were then adopted by a very affluent caucasian couple who lived on the Upper East Side of Manhattan. His new family situation was an uncanny mirror to the plot of Diff’rent Strokes, one of the most popular American TV shows of the early 1980s. In a very short period of time, Kay went from a world where “...

In this special Thanksgiving encore episode, I talk to A.J. Jacobs about his latest book, Thanks a Thousand: A Gratitude Journey, in which he expresses gratitude to a thousand people who are involved with getting him his morning coffee. A.J. Jacobs is an author, journalist, lecturer and human guinea pig. He has written four New York Times bestsellers that combine memoir, science, humor, and a dash...

Rich Beem won the 2002 PGA Championship, one of professional golf’s four major tournaments. Despite having won twice on tour prior to the PGA, Rich's win at Hazeltine was as unlikely as the groovy dance moves he busted out after sinking his final putt of the tournament. Describing himself as “the luckiest guy in the world,” Rich loves golf and hanging out with people who give him energy. He played...

Lisa Birnbach is the author of over 20 books, includingThe Official Preppy Handbook, a cultural phenomenon from the early 1980’s. The book sold more than a million copies and has been cited as an inspiration to the founder of J. Crew and is thought to have boosted the growth of LL Bean.  InT.O.P.H., Birnbach celebrated, skewered, and democratized the concept of preppiness, with writing the The New...

Dr. Brad Klontz is a psychologist and certified financial planner. He helps his clients (many of whom are ultra-high net worth individuals or even billionaires) understand how what they learned about money as kids affects their attitudes and dysfunctions today.  This week, both Paul and his editor/producer extraordinaire Mike Carano take Brad's Money Disorder Assessment and discuss their results i...

Dylan Mohan Gray is the director of The King of Good Times, the pilot film of the new Netflix series, Bad Boy Billionaires: India, which has been the most viewed show in India for much of October. The film chronicles the rise and fall of Vijay Mallya, heir to a brewing fortune and founder of Kingfisher Airlines. Vijay was known for his excessive lifestyle, over-the-top personality, and lavish inve...

Janny Scott grew up on an 800-acre estate near Philadelphia. The descendant of railroad barons and financial magnates, Janny tracks the effects of her family’s multi-generational wealth in her book, The Beneficiary: Fortune, Misfortune, and the Story of My Father. In the book, she lays the details of both the opulence and the tragic complications of her family’s vast resources. While things appear...

Kathy Wang grew up in Northern California and graduated from UC Berkeley and Harvard Business School. After working in the technology field for four years, she quit her job and wrote her first novel, Family Trust, which is the story of the Huangs, a first-generation Chinese-American family. With their father dying and his second wife waiting, the adult kids are wondering what will become of their...